William Wulff
Professor Office: 530 A Chemistry
Phone: 517-355-9715 373 /
Websites: Research Group - Area
Awards & Honors
Genealogy/Graduates
Synthetic Organic Chemistry
(Research Description PDF - 983 kb)Our research areas of interest include methodology development, macrocyclic chemistry, organometallic chemistry, the total synthesis of natural products, supramolecular chemistry and the design and development of new asymmetric catalysts. Several new reactions of transition metal carbene complexes are being studied which have potential applications in natural product synthesis and in the synthesis of non-natural products. An example of the latter is a new entry to the synthesis of calixarenes by the reaction of chromium carbene complexes with acetylenes. This is the first synthesis of calixarenes in which one or more of the four benzene rings are synthesized at the same time as the macrocycle. The same reaction is also being applied to the synthesis of the natural product Phomactin B2, a platelet aggregation factor antagonist. Other synthetic targets for which these reactions are being evaluated include indole alkaloids, steroids, taxol, fostriecin, aureolic acids and Hamigeran B.
Another area of interest involves the development of new chiral ligands for catalysts in asymmetric synthesis. A new family of chiral biaryls has been developed which can be used as chiral ligands for various metal-based Lewis acids that provide chiral catalysts that give asymmetric induction and turnover numbers that are superior to existing catalysts. The evaluation of these ligands in Diels-Alder, Baeyer-Villiger, imino-aldol reactions, heteroatom Diels-Alder reactions and [3+2] cycloadditions are currently being explored as well as their applications to the synthesis of cylindricine and amathaspiramide F. We have recently developed the first generally useful catalytic asymmetric aziridination reaction with a catalyst that was prepared from either the VAPOL or the VANOL ligand. A new program involves the design of chiral macrocycles as catalysts in asymmetric synthesis.
Selected Publications
Regulation of Orthogonal Functions in a Dual Catalyst System. Subservient Role of a Non-chiral Lewis Acid in an Asymmetric Catalytic Heteroatom Diels-Alder Reaction, Newman, C. A.; Antilla, J. C.; Chen, P.; Wulff, W. D., J. Am. Chem. Soc. 2007, 129, 7216-7217.Direct Access to N-H Aziridines from the Asymmetric Catalytic Aziridination with Borate Catalysts Derived from the VANOL and VAPOL Ligands, Lu, Z.; Zhang, Y.; Wulff, W. D., J. Am. Chem. Soc. 2007, 129, 7185-7194.
Total Synthesis of (±)-Phomactin B2 via an Intramolecular Cyclohexadienone Annulation of a Chromium Carbene Complex, Jie Huang, Chunrui Wu and William D. Wulff, J. Am. Chem. Soc. 2007, 129, 13366-13367.
Central-to-Axial Chirality Transfer in the Benzannulation Reaction of Optically Pure Fischer Carbene Complexes in the Synthesis of Allocolchicinoids, Andrei V. Vorogushin, William D. Wulff and Hans-Jürgen Hansen, Tetrahedron 2008, 64, 949-968.
Asymmetric Catalytic Aziridination with Borate Catalysts Derived from the VANOL and VAPOL Ligands ? Scope and Mechanistics Studies, Yu Zhang, Aman Desai, Zhenjie Lu, Gang Hu, Zhensheng Ding and William D. Wulff, Chem. Eur. J. 2008, 3785-3803.
Traceless Stereoinduction in the One-Pot Assembly of all Three Rings of Hexahydrodibenzopyrans, Keith A. Korthals and William D. Wulff, J. Am. Chem. Soc. 2008, 130, 2898-2899.
